Addressing the Configuration Stability of Lithiated Secondary Benzylic Carbamates for the Development of a Noncryogenic Stereospecific Boronate Rearrangement
| Autor: | Heewon Lee, Rolf Schmid, Nelu Grinberg, Daniel R. Fandrick, Keith R. Fandrick, Jinhua J. Song, Adil Duran, Shengli Ma, Joe Gao, Elizabeth Archer, Nathan K. Yee, Jason A. Mulder, Juergen Daeubler, Carl A. Busacca, Michael Konrad, Nitinchandra D. Patel, Chris H. Senanayake, Frederic G. Buono |
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| Rok vydání: | 2014 |
| Předmět: |
chemistry.chemical_classification
Molecular Structure Aryl Organic Chemistry Iodide Substrate (chemistry) Esters Stereoisomerism Boronic Acids Biochemistry chemistry.chemical_compound Stereospecificity chemistry Bromide Benzyl Compounds Organic chemistry Carbamates Physical and Theoretical Chemistry |
| Zdroj: | Organic Letters. 16:4360-4363 |
| ISSN: | 1523-7052 1523-7060 |
| Popis: | A practical noncryogenic process for the Aggarwal stereospecific boronate rearrangement with chiral secondary benzylic carbamates has been developed. The use of LDA instead of sec-BuLi combined with an in situ trapping of the unstable lithiated carbamate was critical to success. Furthermore, this new process increased the substrate scope to include the versatile aryl iodide and bromide substrates. The methodology was applied to a diverse array of substrates and was demonstrated on multikilogram scale. |
| Databáze: | OpenAIRE |
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